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. Author manuscript; available in PMC: 2008 Aug 15.
Published in final edited form as: J Org Chem. 2006 Oct 13;71(21):8183–8189. doi: 10.1021/jo0614902

Table 5.

Effect of Catalyst and Length of Linker on Product Distributiona

Catalyst substrate Δ:ylide E:Zb % yieldc
Rh2(OAc)4 9 100:0 40:60 69
(1.0 mol %) 8 100:0 36:64 71
10 100:0 35:65 68
Rh2(4S-MEOX)4 9 100:0 44:56 39
(1.0 mol %) 8 100:0 65:35 46
10 100:0 n.d. <5
Cu(CH3CN)4PF6 9 56:44 61:39 84
(10 mol %) 8 51:49 57:43 82
10 55:45 47:53 76
Cu(hfacac)2 9 47:53 54:46 63
(10 mol %) 8 52:48 60:40 75
10 51:49 54:46 66
a

Reactions were performed by 2 h addition of the diazoacetate to a refluxing solution of the catalyst in 10 mL of dichloromethane. Outcome from duplicate or triplicate reactions.

b

Ratios of products obtained by integration of characteristic 1H NMR absorbances.

c

Yields were obtained from the mass of the composite isolated products and the integrated 1H NMR signals of cyclopropane and ylide products.